Production process for (poly)alkylene glycol monoalkyl ether

Abstract

The present invention provides a process for producing a (poly)alkylene glycol monoalkyl ether with high selectivity and high yield. In this process, the (poly)alkylene glycol monoalkyl ether is produced by reacting an olefin and a (poly)alkylene glycol in the presence of a catalyst, wherein: 1) a crystalline metallosilicate is used as the catalyst, and at least a portion of the used catalyst is regenerated, and the regenerated catalyst is recycled as the catalyst for the reaction; or 2) the reaction between the olefin and the (poly)alkylene glycol is carried out in the presence of either or both of a (poly)alkylene glycol dialkyl ether and an alcohol.

What is claimed is: 
     
       1. A process for producing a (poly)alkylene glycol monoalkyl ether, comprising the steps of: (1) reacting a (poly)alkylene glycol and an olefin in the presence of a catalyst, thus obtaining the (poly)alkylene glycol monoalkyl ether;   (2) regenerating at least a portion of the used catalyst as used in step (1); and   (3) reacting a (poly)alkylene glycol and an olefin in the presence of a catalyst which includes at least the catalyst as regenerated in the step (2), thus obtaining the (poly)alkylene glycol monoalkyl ether; with the process being characterized in that:     (a) the catalyst is a cystalline metallosilicate; and   (b) step (2) is carried out by thermal treatment within the temperature range of 450 to 900° C. under an oxygen-containing gas atmosphere.   
     
     
       2. A process according to claim 1, wherein the crystalline metallosilicate is a BEA metallosilicate. 
     
     
       3. A process according to claim 1, further comprising the steps of: extracting at least a portion of a slurry containing the catalyst and an unreacted residue of the (poly)alkylene glycol; and recovering the catalyst from the slurry to regenerate the catalyst.   
     
     
       4. A process according to claim 3, further comprising the step of recovering the (poly)alkylene glycol from the slurry by distillation under temperature conditions of 180° C. or lower, when the catalyst is also recovered from the slurry, and with a pressure condition being under that at which the (poly)alkylene boils. 
     
     
       5. A process according to claim 3, further comprising the step of recovering the (poly)alkylene glycol from the slurry by distillation within 30 minutes, when the catalyst is also recovered from the slurry. 
     
     
       6. A process according to claim 1, wherein: the (poly)alkylene glycol monoalkyl ether is a (poly)alkylene glycol mono-higher-alkyl ether; and the olefin is a long chain olefin. 
     
     
       7. A process according to claim 1, wherein the regeneration of at least a portion of the used catalyst is carried out after the catalyst is used for 0.02 to 100 hours for the reaction. 
     
     
       8. A process for producing a (poly)alkylene glycol monoalkyl ether, comprising the steps of: (I) (1) reacting an olefin and a (poly)alkylene glycol in the presence of a catalyst, thus obtaining the (poly)alkylene glycol monoalkyl ether;   (2) regenerating at least a portion of the used catalyst as used in step (1); and   (3) reacting a (poly)alkylene glycol and an olefin in the presence of a catalyst which includes at least the catalyst as regenerated in the step (2), thus obtaining the (poly)alkylene glycol monoalkyl ether; with the process being characterized in that:     (a) the catalyst is a cystalline metallosilicate; and   (b) step (2) is carried out by thermal treatment within the temperature range of 450 to 900° C. under an oxygen-containing gas atmosphere;   (II) separating either or both of a (poly)alkylene glycol dialkyl ether and an alcohol from the resultant (poly)alkylene glycol monoalkyl ether, wherein the (poly)alkylene glycol dialkyl ether and the alcohol are by-products of step (I); and   (III) carrying out an equilibrium reaction of an olefin and a (poly)alkylene glycol with either or both of the (poly)alkylene glycol dialkyl ether and the alcohol which are the by-products as separated in step (II), thus obtaining the (poly)alkylene glycol monoalkyl ether.   
     
     
       9. A process according to claim 8, further comprising the steps of: recovering an unreacted residue of the olefin after the reaction; and   recycling the unreacted residue of the olefin to the reaction with the (poly)alkylene glycol.   
     
     
       10. A process according to claim 8, further comprising the step of recycling a (poly)alkylene glycol phase, resultant from the reaction and including the catalyst, to the reaction with the olefin. 
     
     
       11. A process according to claim 8, wherein: the (poly)alkylene glycol monoalkyl ether is a (poly)alkylene glycol mono-higher-alkyl ether; the olefin is a long chain olefin; the (poly)alkylene glycol dialkyl ether is a (poly)alkylene glycol di-higher-alkyl ether; and the alcohol is a higher alcohol. 
     
     
       12. A process for producing a (poly)alkylene glycol monoalkyl ether, comprising: (I) (1) the step of reacting an olefin and a (poly)alkylene glycol in the presence of a catalyst, thus obtaining the (poly)alkylene glycol monoalkyl ether;   (2) regenerating at least a portion of the used catalyst as used in step (1); and   (3) reacting a (poly)alkylene glycol and an olefin in the presence of a catalyst which includes at least the catalyst as regenerated in the step (2), thus obtaining the (poly)alkylene glycol monoalkyl ether; with the process being characterized in that:     (a) the catalyst is a cystalline metallosilicate; and   (b) step (2) is carried out by thermal treatment within the temperature range of 450 to 900° C. under an oxygen-containing gas atmosphere;   (II) with the process being characterized in that the reaction between the olefin and the (poly)alkylene glycol is carried out in the presence of either or both of a (poly)alkylene glycol dialkyl ether and an alcohol in addition to the (poly)alkylene glycol where said (poly)alkylene glycol dialkyl ether and alcohol are by products of said step of reacting the olefin and the (poly)alkylene glycol.   
     
     
       13. A process according to claim 1, further comprising the steps of: (4) regenerating at least a portion of the catalyst as used in step (3); and   (5) reacting a (poly)alkylene glycol and an olefin in the presence of a catalyst which includes at least the catalyst as regenerated in step (4), thus obtaining the (poly)alkylene glycol monoalkyl ether.   
     
     
       14. A process according to claim 8, further comprising the steps of: (IV) separating either or both of a (poly)alkylene glycol dialkyl ether and an alcohol from the resultant (poly)alkylene glycol monoalkyl ether, wherein the (poly)alkylene glycol dialkyl ether and the alcohol are by-products of step (III); and   (V) carrying out an equilibrium reaction of an olefin and a (poly)alkylene glycol with either or both of the (poly)alkylene glycol dialkyl ether and the alcohol which are the by-products as separated in step (IV), thus obtaining the (poly)alkylene glycol monoalkyl ether.